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Research Articles

Design, Synthesis and Anticancer Evaluation of Novel Bis-Thiazol-1,2,4-Triazine Hybrids Contained 1,3,4-Oxadiazoles

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Pages 7368-7380 | Received 01 Apr 2022, Accepted 04 Oct 2022, Published online: 25 Oct 2022

References

  • G. Lahat, A. Lazar, and D. Lev, “Sarcoma Epidemiology and Etiology: Potential Environmental and Genetic Factors,” The Surgical Clinics of North America 88, no. 3 (2008): 451–81.
  • A.M. Farag, K.M. Dawood, and H.A. Abdel-Aziz, “Synthesis of Some New Pyridazine, 1,2,4-Triazine and 1,3,4-Thiadiazole Derivatives,” Journal of Chemical Research 2004, no. 12 (2004): 808–10.
  • K.M. Dawood, S.M. Moghazy, and A.M. Farag, “Convenient Synthesis of Azolopyrimidine, Azolotriazine, Azinobenzimidazole and 1,3,4-Thiadiazole Derivatives,” Arabian Journal of Chemistry 10 (2017): S2782–S2789.
  • G. Wang, Z. Peng, J. Wang, X. Li, and J. Li, “Synthesis, in-Vitro Evaluation and Molecular Docking Studies of Novel Triazine-Triazole Derivatives as Potential α-Glucosidase Inhibitors,” European Journal of Medicinal Chemistry 125 (2017): 423–9.
  • F. Krauth, H.-M. Dahse, H.-H. Rüttinger, and P. Frohberg, “Synthesis and Characterization of Novel 1,2,4-Triazine Derivatives with Antiproliferative Activity,” Bioorganic & Medicinal Chemistry 18, no. 5 (2010): 1816–21.
  • H. Irannejad, A. Kebriaieezadeh, A. Zarghi, F. Montazer-Sadegh, A. Shafiee, A. Assadieskandar, and M. Amini, “Synthesis, Docking Simulation, Biological Evaluations and 3D-QSAR Study of 5-Aryl-6-(4-Methylsulfonyl)-3-(Metylthio)-1,2,4-Triazine as Selective Cyclooxygenase-2 Inhibitors,” Bioorganic & Medicinal Chemistry 22, no. 2 (2014): 865–73.
  • R.R. Kamble and B.S. Sudha, “Synthesis, Spectral Characterization and Antihaemostatic Activity of 1,2,4-Triazoles Incorporating 1,2,4-Triazine Rings,” Journal of Chemical Sciences 118, no. 2 (2006): 191–4.
  • M.D. Wittman, J.M. Carboni, Z. Yang, F.Y. Lee, M. Antman, R. Attar, P. Balimane, C. Chang, C. Chen, L. Discenza, et al, “Discovery of a 2,4-Disubstituted Pyrrolo[1,2-f][1,2,4]Triazine Inhibitor (BMS-754807) of Insulin-like Growth Factor Receptor (IGF-1R) Kinase in Clinical Development,” Journal of Medicinal Chemistry 52, no. 23 (2009): 7360–3.
  • H. Wang, Z. Zhao, J. Zhou, Y. Guo, G. Wang, H. Hao, and X. Xu, “Corrigendum to a Novel Intestinal-Restricted FXR Agonist,” Bioorganic & Medicinal Chemistry Letters 27, no. 23 (2017): 5353.
  • K. Ban, S. Duffy, Y. Khakham, V.M. Avery, A. Hughes, O. Montagnat, K. Katneni, E. Ryan, and J.B. Baell, “3-Alkylthio-1,2,4-Triazine Dimers with Potent Antimalarial Activity,” Bioorganic & Medicinal Chemistry Letters 20, no. 20 (2010): 6024–9.
  • J.N. Sangshetti and D.B. Shinde, “One Pot Synthesis and SAR of Some Novel 3-Substituted 5,6-Diphenyl-1,2,4-Triazines as Antifungal Agents,” Bioorganic & Medicinal Chemistry Letters 20, no. 2 (2010): 742–5.
  • P. Ahuja and N. Siddiqui, “Anticonvulsant Evaluation of Clubbed Indole-1,2,4-Triazine Derivatives: A Synthetic Approach,” European Journal of Medicinal Chemistry 80 (2014): 509–22.
  • V. Rusinov, I. Egorov, O. Chupakhin, E. Belanov, N. Bormotov, and O. Serova, “Synthesis and Antiviral Activity of 1,2,4-Triazine Derivatives,” Pharmaceutical Chemistry Journal 45, no. 11 (2012): 655–9.
  • M. Khoshneviszadeh, M.H. Ghahremani, A. Foroumadi, R. Miri, O. Firuzi, A. Madadkar-Sobhani, N. Edraki, M. Parsa, and A. Shafiee, “Design, Synthesis and Biological Evaluation of Novel anti-Cytokine 1,2,4-Triazine Derivatives,” Bioorganic & Medicinal Chemistry 21, no. 21 (2013): 6708–17.
  • H. Irannejad, M. Amini, F. Khodagholi, N. Ansari, S.K. Tusi, M. Sharifzadeh, and A. Shafiee, “Synthesis and in Vitro Evaluation of Novel 1,2,4-Triazine Derivatives as Neuroprotective Agents,” Bioorganic & Medicinal Chemistry 18, no. 12 (2010): 4224–30.
  • E.L. Kim, J.L. Li, H.T. Dang, J. Hong, C.-O. Lee, D.-K. Kim, W.D. Yoon, E. Kim, Y. Liu, and J.H. Jung, “Corrigendum to Cytotoxic Cytochalasins from the Endozoic Fungus Phoma sp. of the Giant Jellyfish Nemopilema Nomurai,” Bioorganic & Medicinal Chemistry Letters 22, no. 17 (2012): 5752.
  • R.M. Phillips, “Targeting the Hypoxic Fraction of Tumours Using Hypoxia-Activated Prodrugs,” Cancer Chemotherapy and Pharmacology 77, no. 3 (2016): 441–57.
  • A. Andreani, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi, and M. Rambaldi, “Synthesis and Antitubercular Activity of Imidazo[2,1-b]Thiazoles,” European Journal of Medicinal Chemistry 36, no. 9 (2001): 743–6.
  • S. Bajaj, V. Asati, J. Singh, and P. Roy, “1,3,4-Oxadiazoles: An Emerging Scaffold to Target Growth Factors, Enzymes and Kinases as Anticancer Agents,” European Journal of Medicinal Chemistry 97 (2015): 124–41.
  • M.A. Tantray, I. Khan, H. Hamid, M.S. Alam, A. Dhulap, and A. Kalam, “Synthesis of Benzimidazole-Linked-1,3,4-Oxadiazole Carboxamides as GSK-3β Inhibitors with in Vivo Antidepressant Activity,” Bioorganic Chemistry 77 (2018): 393–401.
  • A.S. Kiselyov, M.N. Semenova, N.B. Chernyshova, A. Leitao, A.V. Samet, K.A. Kislyi, M.M. Raihstat, T. Oprea, H. Lemcke, M. Lantow, et al, “Novel Derivatives of 1,3,4-Oxadiazoles Are Potent Mitostatic Agents Featuring Strong Microtubule Depolymerizing Activity in the Sea Urchin Embryo and Cell Culture Assays,” European Journal of Medicinal Chemistry 45, no. 5 (2010): 1683–97.
  • M. Faheem, A.U. Khan, H. Nadeem, and F. Ali, “Computational and Pharmacological Evaluation of Heterocyclic 1,3,4-Oxadiazole and Pyrazoles Novel Derivatives for Toxicity Assessment, Tumour Inhibition, Antioxidant, Analgesic and Anti-Inflammatory Actions,” Farmacia 66, no. 5 (2018): 909–19.
  • M.D. Altıntop, B. Sever, G. Akalın Çiftçi, G. Turan-Zitouni, Z.A. Kaplancıklı, and A. Özdemir, “Design, Synthesis, in Vitro and in Silico Evaluation of a New Series of Oxadiazole-Based Anticancer Agents as Potential Akt and FAK Inhibitors,” European Journal of Medicinal Chemistry 155 (2018): 905–24.
  • X. Wang, J. Yan, M. Wang, M. Liu, J. Zhang, L. Chen, and W. Xue, “Synthesis and Three-Dimensional Quantitative Structure-Activity Relationship Study of Quinazoline Derivatives Containing a 1,3,4-Oxadiazole Moiety as Efficient Inhibitors against Xanthomonas axonopodis pv,” Molecular Diversity 22, no. 4 (2018): 791–802.
  • J. Chen, Y. Chen, X. Gan, B. Song, D. Hu, and B. Song, “Synthesis, Nematicidal Evaluation, and 3D-QSAR Analysis of Novel 1,3,4-Oxadiazole–Cinnamic Acid Hybrids,” Journal of Agricultural and Food Chemistry 66, no. 37 (2018): 9616–23.
  • Y. Gudi, M.S. Mangali, S. Gundala, P. Venkatapuram, and P. Adivireddy, “Synthesis, Characterization, and Bioassay of a New Class of Pyrazolyl/Isoxazolyl Oxadiazoles,” Monatshefte Für Chemie – Chemical Monthly 149, no. 12 (2018): 2311–26.
  • L. Zhou, P.Y. Wang, J. Zhou, W.B. Shao, H.S. Fang, Z.B. Wu, and S. Yang, “Antimicrobial Activities of Pyridinium-Tailored Pyrazoles Bearing 1,3,4-Oxadiazole Scaffolds,” Journal of Saudi Chemical Society 21, no. 7 (2017): 852–60.
  • P.Y. Wang, L. Chen, J. Zhou, H.S. Fang, Z.B. Wu, B.A. Song, and S. Yang, “Synthesis and Bioactivities of 1-Aryl-4-Hydroxy-1H-Pyrrol-2(5H)-One Derivatives Bearing 1,3,4-Oxadiazole Moiety,” Journal of Saudi Chemical Society 21, no. 3 (2017): 315–23.
  • M. Batool, A. Tajammal, F. Farhat, F. Verpoort, Z. Khattak, M. Shahid, H. Ahmad, M. Munawar, M. Zia-Ur-Rehman, M. Asim Raza Basra, et al, “Molecular Docking, Computational, and Antithrombotic Studies of Novel 1,3,4-Oxadiazole Derivatives,” International Journal of Molecular Sciences 19, no. 11 (2018): 3606.
  • M.S. Tambe, A. Choudhari, D. Sarkar, J. Sangshetti, R. Patil, and S.S. Gholap, “Design, Synthesis and Biological Screening of Novel 1,3,4-Oxadiazoles as Antitubercular Agents,” ChemistrySelect 3, no. 47 (2018): 13304–10.
  • M. Nazir, M.A. Abbasi, S.Z. Siddiqui, K.M. Khan, U. Salar, M. Shahid, M. Ashraf, M. Arif Lodhi, and F. Ali Khan, “New Indole Based Hybrid Oxadiazole Scaffolds with N-Substituted Acetamides: As Potent anti-Diabetic Agents,” Bioorganic Chemistry 81 (2018): 253–63.
  • D. Dewangan, K.T. Nakhate, V.S. Verma, K. Nagori, H. Badwaik, N. Nair, D.K. Tripathi, and A. Mishra, “Synthesis and Molecular Docking Study of Novel Hybrids of 1,3,4-Oxadiazoles and Quinoxaline as a Potential Analgesic and anti-Inflammatory Agents,” Journal of Heterocyclic Chemistry 55, no. 12 (2018): 2901–10.
  • N.D. James and J.W. Growcott, “ZIBOTENTAN Endothelin ETA Receptor Antagonist Oncolytic,” Drugs of the Future 34, no. 8 (2009): 624–33.
  • B. Meunier, “Hybrid Molecules with a Dual Mode of Action: Dream or Reality?,” Accounts of Chemical Research 41, no. 1 (2008): 69–77.
  • A. Pawełczyk, K. Sowa-Kasprzak, D. Olender, and L. Zaprutko, “Molecular Consortia—Various Structural and Synthetic Concepts for More Effective Therapeutics Synthesis,” International Journal of Molecular Sciences 19, no. 4 (2018): 1104.
  • N. Kerru, P. Singh, N. Koorbanally, R. Raj, and V. Kumar, “Recent Advances (2015–2016) in Anticancer Hybrids,” European Journal of Medicinal Chemistry 142 (2017): 179–212.

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